DOE PAGES title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Effect of Alkyl Chain Branching Point on 3D Crystallinity in High N‐Type Mobility Indolonaphthyridine Polymers

Abstract

Abstract Herein, this study investigates the impact of branching‐point‐extended alkyl chains on the charge transport properties of three ultrahigh n‐type mobility conjugated polymers. Using grazing incidence wide‐angle X‐ray scattering, analysis of the crystallinity of the series shows that while π–π interactions are increased for all three polymers as expected, the impact of the side‐chain engineering on polymer backbone crystallinity is unique to each polymer and correlates to the observed changes in charge transport. With the three polymers exhibiting n‐type mobilities between 0.63 and 1.04 cm 2 V −1 s −1 , these results ratify that the indolonaphthyridine building block has an unprecedented intrinsic ability to furnish high‐performance n‐type organic semiconductors.

Authors:
 [1];  [1];  [2];  [3];  [1];  [1];  [1];  [4];  [3];  [5];  [2];  [1]
  1. Department of Chemistry University College London Christopher Ingold Building London WC1H 0AJ UK
  2. Centre for Plastic Electronics Imperial College London London SW7 2AZ UK
  3. Chemical Sciences and Engineering Division Argonne National Laboratory 9700 South Cass Avenue Lemont IL 60439 USA, Department of Chemistry Materials Research Center and Argonne‐Northwestern Solar Energy Research Center Northwestern University 2145 Sheridan Road Evanston IL 60208 USA
  4. Department of Chemistry Texas A&,M University at Qatar P.O. Box 23874 Doha Qatar
  5. Department of Chemistry Materials Research Center and Argonne‐Northwestern Solar Energy Research Center Northwestern University 2145 Sheridan Road Evanston IL 60208 USA
Publication Date:
Sponsoring Org.:
USDOE
OSTI Identifier:
1395407
Grant/Contract Number:  
DE‐AC02‐06CH11357
Resource Type:
Publisher's Accepted Manuscript
Journal Name:
Advanced Functional Materials
Additional Journal Information:
Journal Name: Advanced Functional Materials Journal Volume: 27 Journal Issue: 43; Journal ID: ISSN 1616-301X
Publisher:
Wiley Blackwell (John Wiley & Sons)
Country of Publication:
Germany
Language:
English

Citation Formats

Fallon, Kealan J., Santala, Annikki, Wijeyasinghe, Nilushi, Manley, Eric F., Goodeal, Niall, Leventis, Anastasia, Freeman, David M. E., Al‐Hashimi, Mohammed, Chen, Lin X., Marks, Tobin J., Anthopoulos, Thomas D., and Bronstein, Hugo. Effect of Alkyl Chain Branching Point on 3D Crystallinity in High N‐Type Mobility Indolonaphthyridine Polymers. Germany: N. p., 2017. Web. doi:10.1002/adfm.201704069.
Fallon, Kealan J., Santala, Annikki, Wijeyasinghe, Nilushi, Manley, Eric F., Goodeal, Niall, Leventis, Anastasia, Freeman, David M. E., Al‐Hashimi, Mohammed, Chen, Lin X., Marks, Tobin J., Anthopoulos, Thomas D., & Bronstein, Hugo. Effect of Alkyl Chain Branching Point on 3D Crystallinity in High N‐Type Mobility Indolonaphthyridine Polymers. Germany. https://doi.org/10.1002/adfm.201704069
Fallon, Kealan J., Santala, Annikki, Wijeyasinghe, Nilushi, Manley, Eric F., Goodeal, Niall, Leventis, Anastasia, Freeman, David M. E., Al‐Hashimi, Mohammed, Chen, Lin X., Marks, Tobin J., Anthopoulos, Thomas D., and Bronstein, Hugo. Thu . "Effect of Alkyl Chain Branching Point on 3D Crystallinity in High N‐Type Mobility Indolonaphthyridine Polymers". Germany. https://doi.org/10.1002/adfm.201704069.
@article{osti_1395407,
title = {Effect of Alkyl Chain Branching Point on 3D Crystallinity in High N‐Type Mobility Indolonaphthyridine Polymers},
author = {Fallon, Kealan J. and Santala, Annikki and Wijeyasinghe, Nilushi and Manley, Eric F. and Goodeal, Niall and Leventis, Anastasia and Freeman, David M. E. and Al‐Hashimi, Mohammed and Chen, Lin X. and Marks, Tobin J. and Anthopoulos, Thomas D. and Bronstein, Hugo},
abstractNote = {Abstract Herein, this study investigates the impact of branching‐point‐extended alkyl chains on the charge transport properties of three ultrahigh n‐type mobility conjugated polymers. Using grazing incidence wide‐angle X‐ray scattering, analysis of the crystallinity of the series shows that while π–π interactions are increased for all three polymers as expected, the impact of the side‐chain engineering on polymer backbone crystallinity is unique to each polymer and correlates to the observed changes in charge transport. With the three polymers exhibiting n‐type mobilities between 0.63 and 1.04 cm 2 V −1 s −1 , these results ratify that the indolonaphthyridine building block has an unprecedented intrinsic ability to furnish high‐performance n‐type organic semiconductors.},
doi = {10.1002/adfm.201704069},
journal = {Advanced Functional Materials},
number = 43,
volume = 27,
place = {Germany},
year = {Thu Sep 28 00:00:00 EDT 2017},
month = {Thu Sep 28 00:00:00 EDT 2017}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record
https://doi.org/10.1002/adfm.201704069

Citation Metrics:
Cited by: 18 works
Citation information provided by
Web of Science

Save / Share:

Works referenced in this record:

Exploring the origin of high optical absorption in conjugated polymers
journal, May 2016

  • Vezie, Michelle S.; Few, Sheridan; Meager, Iain
  • Nature Materials, Vol. 15, Issue 7
  • DOI: 10.1038/nmat4645

Unconventional Face-On Texture and Exceptional In-Plane Order of a High Mobility n-Type Polymer
journal, July 2010

  • Rivnay, Jonathan; Toney, Michael F.; Zheng, Yan
  • Advanced Materials, Vol. 22, Issue 39
  • DOI: 10.1002/adma.201001202

Thieno[3,2- b ]thiophene−Diketopyrrolopyrrole-Containing Polymers for High-Performance Organic Field-Effect Transistors and Organic Photovoltaic Devices
journal, March 2011

  • Bronstein, Hugo; Chen, Zhuoying; Ashraf, Raja Shahid
  • Journal of the American Chemical Society, Vol. 133, Issue 10
  • DOI: 10.1021/ja110619k

Recent Advances in Bulk Heterojunction Polymer Solar Cells
journal, August 2015


A high-mobility electron-transporting polymer for printed transistors
journal, January 2009

  • Yan, He; Chen, Zhihua; Zheng, Yan
  • Nature, Vol. 457, Issue 7230, p. 679-686
  • DOI: 10.1038/nature07727

The Role of Regioregularity, Crystallinity, and Chain Orientation on Electron Transport in a High-Mobility n-Type Copolymer
journal, March 2014

  • Steyrleuthner, Robert; Di Pietro, Riccardo; Collins, Brian A.
  • Journal of the American Chemical Society, Vol. 136, Issue 11
  • DOI: 10.1021/ja4118736

Diketopyrrolopyrrole–Diketopyrrolopyrrole-Based Conjugated Copolymer for High-Mobility Organic Field-Effect Transistors
journal, October 2012

  • Kanimozhi, Catherine; Yaacobi-Gross, Nir; Chou, Kang Wei
  • Journal of the American Chemical Society, Vol. 134, Issue 40
  • DOI: 10.1021/ja308211n

Photocurrent Enhancement from Diketopyrrolopyrrole Polymer Solar Cells through Alkyl-Chain Branching Point Manipulation
journal, July 2013

  • Meager, Iain; Ashraf, Raja Shahid; Mollinger, Sonya
  • Journal of the American Chemical Society, Vol. 135, Issue 31
  • DOI: 10.1021/ja406934j

A Naphthodithiophene-Diketopyrrolopyrrole Donor Molecule for Efficient Solution-Processed Solar Cells
journal, June 2011

  • Loser, Stephen; Bruns, Carson J.; Miyauchi, Hiroyuki
  • Journal of the American Chemical Society, Vol. 133, Issue 21
  • DOI: 10.1021/ja202791n

Side-Chain-Induced Rigid Backbone Organization of Polymer Semiconductors through Semifluoroalkyl Side Chains
journal, January 2016

  • Kang, Boseok; Kim, Ran; Lee, Seon Baek
  • Journal of the American Chemical Society, Vol. 138, Issue 11
  • DOI: 10.1021/jacs.5b10445

Investigation of Structure–Property Relationships in Diketopyrrolopyrrole-Based Polymer Semiconductors via Side-Chain Engineering
journal, February 2015

  • Back, Jang Yeol; Yu, Hojeong; Song, Inho
  • Chemistry of Materials, Vol. 27, Issue 5
  • DOI: 10.1021/cm504545e

Design, Synthesis, and Structure–Property Relationships of Isoindigo-Based Conjugated Polymers
journal, February 2014

  • Lei, Ting; Wang, Jie-Yu; Pei, Jian
  • Accounts of Chemical Research, Vol. 47, Issue 4
  • DOI: 10.1021/ar400254j

Molecular origin of high field-effect mobility in an indacenodithiophene–benzothiadiazole copolymer
journal, July 2013

  • Zhang, Xinran; Bronstein, Hugo; Kronemeijer, Auke J.
  • Nature Communications, Vol. 4, Issue 1
  • DOI: 10.1038/ncomms3238

Indolo-naphthyridine-6,13-dione Thiophene Building Block for Conjugated Polymer Electronics: Molecular Origin of Ultrahigh n-Type Mobility
journal, November 2016


Scherrer grain-size analysis adapted to grazing-incidence scattering with area detectors
journal, October 2009


A Nature-Inspired Conjugated Polymer for High Performance Transistors and Solar Cells
journal, July 2015


Chalcogenophene Comonomer Comparison in Small Band Gap Diketopyrrolopyrrole-Based Conjugated Polymers for High-Performing Field-Effect Transistors and Organic Solar Cells
journal, January 2015

  • Ashraf, Raja Shahid; Meager, Iain; Nikolka, Mark
  • Journal of the American Chemical Society, Vol. 137, Issue 3
  • DOI: 10.1021/ja511984q

Polymer solar cells with enhanced fill factors
journal, August 2013


Long and winding polymeric roads
journal, October 2013


High-Molecular-Weight Regular Alternating Diketopyrrolopyrrole-based Terpolymers for Efficient Organic Solar Cells
journal, June 2013

  • Hendriks, Koen H.; Heintges, Gaël H. L.; Gevaerts, Veronique S.
  • Angewandte Chemie International Edition, Vol. 52, Issue 32
  • DOI: 10.1002/anie.201302319